(2-Methoxyethyl)(methyl)amine → 1-(7-Fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-N-(2-methoxyethyl)-N,3,3-trimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-amine

HRID 1618529Notes

Reaction equation

HRID 1618529 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:10]([C:11]3[C:20]4[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=4)[N:14]=[C:13]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)[C:12]=3[CH3:28])[CH2:9][C:8]([CH3:30])([CH3:29])[C:5]2=[N:6][CH:7]=1.[CH3:31][O:32][CH2:33][CH2:34][NH:35][CH3:36].CC(C)([O-])C.[Na+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:21][C:17]1[CH:16]=[C:15]2[C:20]([C:11]([N:10]3[C:4]4[C:5](=[N:6][CH:7]=[C:2]([N:35]([CH2:34][CH2:33][O:32][CH3:31])[CH3:36])[CH:3]=4)[C:8]([CH3:29])([CH3:30])[CH2:9]3)=[C:12]([CH3:28])[C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[N:14]2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 672855904-(6-Bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline

Product 1

HCID 509389511-(7-Fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-N-(2-methoxyethyl)-N,3,3-trimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-amine

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

Prepared according to procedure N using 4-(6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (80 mg, 0.17 mmol), Pd2dba3 (15.8 mg, 0.017 mmol), N-(2-methoxyethyl)methylamine (15.4 mg, 0.17 mmol), sodium tert-butoxide (33.2 mg, 0.34 mmol) and XPhos (16.5 mg, 0.035 mmol) and heating in the microwave for 2 h at 120° C. After purification 1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-N-(2-methoxyethyl)-N,3,3-trimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-amine was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 8.69-8.79 (1H, m), 7.75-7.98 (4H, m), 7.45 (1H, dd, J=2.1, 1.7 Hz), 7.37-7.43 (1H, m, J=7.4, 4.8, 1.5, 1.5 Hz), 7.28-7.33 (1H, m), 5.62-5.75 (1H, m), 3.73-3.87 (2H, m), 3.38-3.45 (2H, m), 3.29-3.35 (2H, m), 3.24 (3H, d, J=1.4 Hz), 2.84 (3H, d, J=1.4 Hz), 2.38 (3H, s), 1.61 (3H, s), 1.55 (3H, s). Mass Spectrum (ESI) m/e=472 (M+1).

Workup

  1. customPrepared
  2. customAfter purification 1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-N-(2-methoxyethyl)-N,3,3-trimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-amine
  3. customwas obtained as a yellow film

Sources & evidence

ORD record
ord-163c8b3b900942679e03efd02a9d2717
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

Loading…